CN1106146C - P-hydroxy-phenylacetic acid for reducing anti-repelling properties of insecticide - Google Patents
P-hydroxy-phenylacetic acid for reducing anti-repelling properties of insecticide Download PDFInfo
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- CN1106146C CN1106146C CN96112296A CN96112296A CN1106146C CN 1106146 C CN1106146 C CN 1106146C CN 96112296 A CN96112296 A CN 96112296A CN 96112296 A CN96112296 A CN 96112296A CN 1106146 C CN1106146 C CN 1106146C
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/002—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing a foodstuff as carrier or diluent, i.e. baits
- A01N25/006—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing a foodstuff as carrier or diluent, i.e. baits insecticidal
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
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- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Insects & Arthropods (AREA)
- Food Science & Technology (AREA)
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to the new use of p-hydroxyphenylacetic acid, by itself or in a mixture with other chemical compounds, for reducing the repellency of insecticides in the control of cockroaches, and to cockroach control compositions which comprise these mixtures, details being found in the description.
Description
The present invention relates to the new purposes of p-hydroxyphenylaceticacid, this new purposes is to reduce insecticide by itself or with the mixture of other compounds, particularly prevent and treat the anti-repelling properties of insecticide of cockroach, and the control composition of cockroach that wherein contains the mixture of p-hydroxyphenylaceticacid and this carboxylic acid and other compounds.
In room and commerce, infecting of cockroach is a quite serious hygienic issues, in many cases, is essential to the control of cockroach., because the life type of cockroach is very difficult to their control.Wherein a special problem of Cun Zaiing is, many in practice insecticides have anti-repelling properties, and this has just reduced the success rate of control.
M.K.Rust and D.A.Reierson (Journal of Economic Entomology 70 (1) (1977), 34-38) extract of using cockroach ight soil has been described, improving the activity of chlopyrifos, unden, basudin and Dri-Die, and this effect that reduces as these anti-repelling properties of insecticide has been discussed.
A.E.Glaser (International Pest Control 22 (1) (1980), 7-8 21) has described the same phenomenon that sumithion is occurred.
Yet said method is unsuitable for commercial use, because by extracting the ight soil of cockroach, have only a spot of anti-repellent material to provide as insecticide.
Surprisingly, have now found that the p-hydroxyphenylaceticacid compound of following formula (I)
No matter with itself or with the form of the mixture of other compounds, all similar to dark dung beetle stool extract, reduced anti-repelling properties of insecticide, and therefore in the control of cockroach, can very well use.
Reduced the repellent action of insecticide according to the mixture of anti-anti-repelling properties p-hydroxyphenylaceticacid of the present invention and itself and other compound.Particularly pyrethroid is to the repellent action of cockroach, and therefore increased the effect of the chemical control composition of insect.
According to known and stable formula of the present invention (I) compound, with itself and with the form of the mixture of other compounds, in the chemical control composition of insect, have very high activity, and be preferred for bait and spray application.
Formula (I) compound can acid form, form that also can its salt is used.Can also its free acid and the form use of the mixture of specific salt.
The alkali of specific salt that can be used to prepare hydroxyl phenylacetic acid is all commonly used in chemical active compound, preferred as alkali, alkaline earth metal, ammonium, alkylammonium, dialkyl ammonium, trialkyl ammonium or tetraalkylammonium hydroxides, more preferably sodium, potassium, calcium or ammonium oxygen oxide, and be preferably sodium hydroxide especially.
Can use mixture control cockroach according to formula of the present invention (I) compound and/or itself and other compound, it is Lian purpose insect, the insect of Lian section particularly, preferred Groton bug or big Lian section, preferred east Lian and American cockroach, and also prevent and treat the cockroach of other kinds, particularly preferably be the control Groton bug.
Reduced cockroach to the insecticide repellent action of pyrethroid for example according to the mixture of formula of the present invention (I) compound and/or itself and other compound.
The above-mentioned puberty (larva, adult) that acts on the various variations of cockroach all exists.In cockroach prevention and cure,, can use the mixture of p-hydroxyphenylaceticacid and/or itself and other compound easily regardless of the kind of the method for using of preventing and treating.Preferably can use it in the chemical prevention and control method, and if be fit to and other activating agents, as lure bait or other attractants, synthetic or naturally occurring agrochemical to use together.
By thinking or research simply simply, possible is determines the mixture used for specific application target and type and amount of application preferably by the expert.
Preferably use the mixture of p-hydroxyphenylaceticacid and/or itself and other compound with the spray pattern of routine.Can use normally used spraying equipment when using conventional formulation.Also can be with the mixture of p-hydroxyphenylaceticacid and/or itself and other compound, if be fit to, being mixed with the mixture of suitable insecticide can be by the pulvis of spreading or granule.The preferred every m of amount of application of p-hydroxyphenylaceticacid and/or itself and other compound
20.1 to 500mg, and more preferably every m
21 to 200mg (based on p-hydroxyphenylaceticacid).
When being used for containing the bait of insecticide, p-hydroxyphenylaceticacid and/or its are mixed with bait with the mixture of other compounds or using (for example at its top) near bait.The form (sustained release preparation) that the mixture of p-hydroxyphenylaceticacid and/or itself and other compound can also discharge in considerable time exists.For example, for this reason, they can be incorporated in polymeric material, paraffin, the wax etc., or exist with microencapsulation form.Spendable conventional equipment is a trap, and the pharmaceutical substance of the feed of luring usually is a bait.The preferred usage amount of the mixture of p-hydroxyphenylaceticacid and/or itself and other compound is that every gram bait is 0.0001 to 100mg (more preferably 0.01 to 20mg) (based on p-hydroxyphenylaceticacid).
The invention still further relates to the composition of control cockroach, it comprises if be fit to, except the carrier and auxiliary agent and/or other additives (as bait or attractant) of routine, comprising p-hydroxyphenylaceticacid and/or itself and other compound and mixture and at least a insecticide active substance, p-hydroxyphenylaceticacid and/or its can be mixed with other components with the mixture of other compounds or exist with the form of separating placement.
Other compounds mean, organic carboxyl acid particularly, preferred especially benzoic acid, phenylacetic acid, ortho-aminobenzoic acid, 3-(hydroxy phenyl) propionic acid, 3-(p-hydroxybenzene) propionic acid, 2 hydroxy propanoic acid, capric acid, palmitic acid, stearic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, methyl pimelic acid, fumaric acid or maleic acid.
The insect killing substance that can be used is activated to cockroach, and insecticide active substance and according to the various materials of no illeffects between p-hydroxyphenylaceticacid of the present invention or the mixture.
For example, insecticide active substance can belong to the phosphate of insecticidal activity, carbamate, naturally occurring pyrethrins and close penta pyrethroid, guanylhydrazones, sulphamide, nitro imino group, Nitromethylene, cyanoimino or cyano group methylene compound, pyrrolidines-2, the 4-derovatives, pyrazoline derivative, Olivomitecidin (avermectin and ivermecfin) derivative, i.e. chinaberry element, annonines and/or Ryanicide.
Also may use chitin synthesis inhibitor (for example triflumeron, duflubenzuron, Lufenuron, flufenoxuron etc.), and juvenile hormone and mimicry element (for example: Entocon ZR 515, Entocon ZR 512, ABG-6215, pyriproxyfen etc.) or " General Medicine " (boron, yeast, toast bread powder etc.).
Below can narrate the insecticide that the mixture of according to the present invention particularly preferred and p-hydroxyphenylaceticacid and/or its and other compound is prepared:
1) the formamide acid esters of formula (II)
Wherein
R
1Carbocylic radical or heterocyclic aryl that representative replaces arbitrarily, or any oximido that replaces of representative will describe preferred R in detail below
1Group,
R
2Represent C
1-C
4Alkyl and
R
3Represent hydrogen or C
1-C
4Alkyl, or represent group U, wherein
U representative-CO-R
4Base, wherein
R
4Represent halogen, C
1-C
4Alkyl, C
1-C
4Alkoxyl, C
3-C
5Alkenyloxy, C
3-C
5Chain oxy-acetylene, C
1-C
4Alkylthio group, C
1-C
4Alkyl amino, two C
1-C
4Alkyl amino or C
1-C
4Alkyl hydroxy amino, or
Represent phenoxy group, thiophenyl or phenyl amino, they are at random by halogen, nitro, cyano group, trifluoromethyl, C
1-C
4Alkyl, C
1-C
4Alkoxyl, C
1-C
4Alkylene dioxo base, C
1-C
4Alkylthio group or C
1-C
4Alkoxy carbonyl replaces, or
Represent 2,3-dihydro-2,2-dimethyl-7-benzofuranyl or represent the group of following formula
Wherein
R
5Represent hydrogen, C
1-C
4Alkyl or two C
1-C
4Alkyl amino-carbonyl and
R
6Represent C
1-C
4Alkyl, C
1-C
4Alkylthio group, cyano group C
1-C
4Alkylthio group or C
1-C
4Alkylthio group C
1-C
4Alkyl;
Or two R
5And R
6Group is represented together at random by oxygen, sulphur, SO or SO
2The C that is interrupted
2-C
8Alkane two bases, or
Wherein
U represents group-S
v(O)
w-R
7, wherein
V represents 1 or 2 Hes
W represents 0,1 or 2, wherein under V is 2 situation, w represents 0,
R
7Represent C
1-C
4Alkyl, C
3-C
5Alkenyl, C
3-C
5Alkynyl group or C
3-C
6Cycloalkyl, they can at random be replaced by halogen, or represent phenyl, benzyl or phenethyl, they can be at random by halogen, cyano group, nitro, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, C
1-C
4Alkyl or C
1-C
4Alkoxyl replaces, or represents the group of following formula
Wherein
R
8Represent C
1-C
4Alkyl, C
3-C
5Alkenyl, C
3-C
5Alkynyl group, C
3-C
6Cycloalkyl or benzyl and
R
9Represent C
1-C
4Alkyl, C
3-C
5Alkenyl, C
3-C
5Alkynyl group, C
3-C
6Cycloalkyl, benzyl, phenethyl, halo carbonyl, formoxyl, C
1-C
4Alkyl-carbonyl, C
1-C
4Alkoxy carbonyl, C
1-C
4Alkoxyl phenyloxycarbonyl, C
3-C
5Chain oxy-acetylene carbonyl, C
3-C
5Alkenyloxy carbonyl, C
1-C
4Alkylthio group carbonyl, C
1-C
4Alkyl amino-carbonyl, C
1-C
4Alkyl hydroxy amino carbonyl, C
1-10The alkyl phenoxy carbonyl ,=C
1-C
4Alkyl amino-carbonyl, thiophenyl carbonyl, phenyloxycarbonyl or 2; 3-dihydro-2; 2-dimethyl-7-benzofuran oxygen base carbonyl, or represent thiophenyl, phenylsulfinyl base, benzenesulfonyl or phenyl, they can be at random by halogen, cyano group, nitro, trifluoromethyl, C
1-C
10Alkyl or C
1-C
4Alkoxyl replaces, or represents the following formula group
Wherein
R
10Has above-mentioned R
5The definition that provides and
R
11Has above-mentioned R
6The definition that provides, in addition, wherein, at group
In, radicals R
8And R
9The representative hydrocarbon chain that has 3 to 8 carbon atoms and can be at random be interrupted by oxygen or sulphur atom together, and R wherein
7Also can represent group S
v(O)
w-R
7The identical group that is bonded.Particularly preferred reactive compound component is the carbamate of formula II, wherein
R
1Representative is by phenyl, naphthyl, 2, one group of group that 3-dihydro-7-benzofuranyl, pyrazolyl or pyrimidine radicals are formed, and above-mentioned group can be at random by C
1-C
4Alkyl, C
2-C
4Alkenyl, C
1-C
4Alkoxyl, C
1-C
4Alkoxy methyl, C
1-C
4Alkylthio group, C
1-C
4Alkylthio group methyl, C
1-C
4Alkyl amino, two (C
1-C
4Alkyl) amino, two (C
3-C
4Alkenyl) amino, halogen, dioxolanyl, methylene-dioxy and/or by group-N=CH-N (CH
3)
2Replace, or wherein
R
1Represent the alkylidene amino of following formula
Wherein
R
12And R
13Has above-mentioned R
5And R
6The definition that provides respectively,
R
2Represent C
1-C
4Alkyl and
R
3Represent hydrogen or C
1-C
4Alkyl (preferred hydrogen).The example of the carbamate of the formula that can narrate (II) is following N-methyl carbamate: the 2-aminomethyl phenyl, the 2-ethylphenyl, the 2-isopropyl phenyl, the 2-secondary butyl phenenyl, the 2-methoxyphenyl, the 2-ethoxyl phenenyl, the 2-isopropyl phenyl, the 4-aminomethyl phenyl, the 4-ethylphenyl, 4-n-pro-pyl phenyl, the 4-methoxyphenyl, the 4-ethoxyl phenenyl, 4-positive propoxy phenyl, 3,4, the 5-trimethylphenyl, 3,5-dimethyl-4-methyl mercapto phenyl, 3-methyl-4-dimethylaminophenyl, 2-ethylmercapto group aminomethyl phenyl, the 1-naphthyl, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl, 2,3-(dimethylated methylene dioxy base) phenyl, 2-(4,5-dimethyl-1,3-dioxolanes-1-yl) phenyl, 1-methyl mercapto ethyleneimino, 2-methyl mercapto-2-methyl propylidene amino, 1-(2-cyano group ethylmercapto group) ethyleneimino and 1-sulfurous ylmethyl-2, the N-methyl carbamate of 2-dimethyl propylidene amino, preferred N-methyl carbamic acid 2-isopropyl phenyl ester.2) carboxylate of formula (III)
Wherein,
R
14Represent the open chain alkyl or cycloalkyl, itself or at random replaced by following radicals: halogen, alkyl or cycloalkyl, or the alkenyl that is at random replaced by halogen, alkyl and/or alkoxyl, or at random by the phenyl or the styryl of halogen or halogenic substituent (it is made up of alkyl, alkoxyl, alkylene dioxo base and/or alkylthio group) replacement arbitrarily, or the cycloalkenyl (it is by benzo-fused arbitrarily) of any halogen replacement of volution connection, and wherein
R
15Represent hydrogen, alkyl, haloalkyl, alkenyl, alkynyl group or cyano group and
R
16Represent the alkyl or aryl that replaces arbitrarily or represent heterocyclic radical, or and R
15The carbon atom of two groups that wherein are bonded forms the cyclopentanone ring together.
Particularly preferred reactive compound component is the carboxylate of formula (III), wherein (a) R
14Represent group
Wherein
R
17Represent hydrogen, methyl, fluorine, chlorine or bromine and
R
18Represent methylidene, fluorine, chlorine, bromine, C
1-C
2Fluoroalkyl or C
1-C
2Chlorofluoromethane base, or represent phenyl, its arbitrarily by halogen and/or arbitrarily halogenic substituent (it is by C
1-C
4Alkyl, C
1-C
4Alkoxyl, C
1-C
4Alkylthio group and/or C
1-C
2Alkylene dioxo base is formed), or R wherein
7And R
8Two groups are represented C
2-C
5Alkane two bases (alkylidene):
Or b wherein) R
14Represent group
Wherein
R
19Represent phenyl, (it is by C by the halogen group of halogen and/or replacement arbitrarily arbitrarily for it
1-C
4Alkyl, C
1-C
4Alkoxyl, C
1-C
4Alkylthio group or C
1-C
2Alkylene dioxo base is formed) replace and
R
20Represent isopropyl or cyclopropyl;
Or c wherein) R
14One of represent methylidene or following radicals
Two keys of expressing possibility of dotted line and wherein wherein
R
14Represent hydrogen, C
1-C
4Alkyl, C
1-C
4Haloalkyl, cyano group or acetenyl and
R
16The group that representative is made up of phenyl, furyl and tetrahydrochysene phthalimido, wherein above-mentioned group can be by halogen and/or by C
1-C
4Alkyl, C
2-C
4Alkenyl, C
1-C
4Alkoxyl, C
2-C
4Alkenyloxy, C
1-C
4Alkylthio group, C
1-C
2One group of group (can be replaced by halogen again in them) that alkylene dioxo base, phenoxy group and/or benzyl are formed replaces, and R wherein
6Preferably represent tetrafluoro phenyl, 3,4-dichlorophenyl or tetrahydrochysene phthalimido, or the Phenoxyphenyl that on a phenyl ring or two phenyl ring, replaced of representative by halogen (preferred fluorine).Naturally occurring pyrethroid (as Dalmatian chrysanthemum) or synthetic pyrethroid are particularly preferred formula (III) carboxylates.
The example of particularly preferred formula (III) carboxylate can be described below according to the present invention: 3,4,5,6-tetrahydrochysene phthalimido methyl 2,2-dimethyl-3-(2-metering system-1-yl) cyclopropane carboxylic acid ester, 3-benzyloxy phenoxy base 2,2-dimethyl-3-(2, the 2-dichloroethylene) cyclopropyl carboxylic acid esters, 2-cyano group-3-phenoxy benzyl 2,2-dimethyl-3-(2, the 2-dichloroethylene) cyclopropanecarboxylcompound, alpha-cyano-4-fluoro-3-phenoxy benzyl 2,2-dimethyl-3-(2, the 2-dichloroethylene) cyclopropanecarboxylcompound, 2,3,5,6-ptfe benzyl 2,2-dimethyl-3-(2, the 2-dichloroethylene) cyclopropanecarboxylcompound, alpha-cyano-3-phenoxy benzyl 2,2-dimethyl-3-(2, the 2-dibromo vinyl) cyclopropanecarboxylcompound and alpha-cyano-3-phenoxy benzyl 3-methyl-2-(4-chlorphenyl) butyrate.3) phosphate or the phosphonate ester of formula (IV)
Wherein
A be identical or different and represent O or S and
B represent O, S or-NH-, or represent center P atom and R
23Between direct key and
R
21And R
22Be identical or different and alkyl or aryl that representative replaces arbitrarily and,
R
23The alkyl, aryl, heteroaryl, aralkyl, alkenyl or dioxanes base or the oximido that represent hydrogen, replace arbitrarily, or representative is bonded the identical group on it.Above-mentioned particularly preferred formula (IV) phosphate and phosphonate ester are following radicals, wherein
R
21And R
22Be identical or different and represent C
1-C
4Alkyl or phenyl,
R
23Represent hydrogen; or representative has the alkyl of 1 to 4 carbon atom; it is arbitrarily by halogen, hydroxyl, cyano group, the phenyl, carbamoyl, alkyl sulphonyl, alkyl sulfinyl, alkyl-carbonyl, alkoxyl, alkylthio group, the alkoxy carbonyl that replace of halogen or have in all cases nearly that the alkyl amino-carbonyl of 6 carbon atoms replaces arbitrarily
R
23Also representative has the nearly alkenyl of 4 carbon atoms, phenyl or C that it is replaced by halogen arbitrarily
1-C
4Alkoxy carbonyl replaces, or
R
23The group of the following general formula of representative
R wherein
24And R
25Has above-mentioned R
5And R
6The definition that provides, or represent cyano group or phenyl,
R
23Also represent the dioxanes base, it can be bonded to R
22Identical group replace or R
23Representative is bonded to the identical group on it, or R
23Represent phenyl, it is replaced by methyl, nitro, cyano group, halogen and/or methyl mercapto arbitrarily, and wherein
R
23Also particularly preferably represent heteroaryl, as pyridine radicals, quinolyl, quinoxalinyl, pyrimidine radicals or phendioxin, 2, the 4-triazinyl, they are arbitrarily by C
1-C
4Alkoxyl, C
1-C
4Alkylthio group methyl, C
1-C
4Alkyl and/or halogen replace.
Followingly be stated as particularly: O, the O-dimethyl, O, O-diethyl-O-(2,2-dichloro and 2, the 2-dibromo vinyl) phosphate, O, O-diethyl-O-(4-nitrobenzophenone) thion phosphate, O, O-dimethyl-O-(3-methyl-4-methyl mercapto phenyl), the thion phosphate, O, O-dimethyl-O-(3-methyl-4-nitrobenzophenone) thion phosphate, O-ethyl-S-n-pro-pyl-O-(2,4 dichloro benzene base) thion phosphate, O-ethyl-S-n-pro-pyl-O-(4-methyl mercapto phenyl) thion phosphate, O, O-dimethyl-S-(4-oxo-1,2,3-phentriazine-3-base-methyl) thion phosphate, O-methyl-O-(2-isopropyl-6-methoxy pyrimidine-4-yl) thion methane phosphate, O, O-diethyl-O-(2-isopropyl-6-methylpyrimidine-4-yl) thion phosphate, O, O-diethyl-O-(the thion phosphate of 3-chloro-4-methyl-coumarin-7-yl), O, O-dimethyl-2,2,2-three chloro-1-hydroxyl ethane phosphates, O, O-dimethyl-S-(methylamino carbonyl methyl) thion phosphate O-methyl-O-(the 6-methoxyl group-2-tert-butyl group) pyrimidine-4-yl) thion ethane phosphate.4) Nitromethylene of formula (V), nitro imino group, cyanoimino or cyano group methylene derivatives
Wherein
R
26Represent C
1-C
4Alkyl (preferable methyl or ethyl), or represent group
Wherein
R
30Represent C
1-C
4Alkyl (preferable methyl or ethyl), or
R
30With R
27The C an of-any side chain of representative
2-C
5Alkane two basic chains are (preferred-(CH
2)
2-or-(CH
2)
3-) and
R
31Represent hydrogen or C
1-C
4Alkyl (preferred hydrogen),
R
27Represent C
1-C
4Alkyl (preferable methyl or ethyl), or and R
30Represent the C of any side chain together
2-C
5Alkane two basic chains are (preferred-(CH
2)
2-or-(CH
2)
3-)
R
28Represent NO
2Or CN,
R
29Representative replace arbitrarily (preferably by halogen and/or C
1-C
4Alkyl replaces) heteroaryl (preferred pyridine radicals) (R wherein
29Especially preferably represent 2-chloropyridine-5-yl)
Q representative=C-or-N-and
V represents direct key, or represents C
1-C
3Alkylene two bases are (preferred-CH
2-).
Mode with example specifically lists some particularly preferred formula (V) compounds as follows:
R wherein
32Representative
Base is in the definition of above-mentioned general formula and group, and above-mentioned group has following general and preferred definition:
Alkyl itself or in alkoxyl or alkoxy carbonyl group, represent to have 1 to 5 as the alkyl of component, preferred 1 to 4 and the straight or branched alkyl of preferred especially 1 to 3 carbon atom, wherein can narrate especially be methyl, ethyl, just and just with isopropyl, different, second month in a season and the tert-butyl group, and wherein methyl and ethyl, particularly methyl are selected especially.
In the phenyl, phenoxy group or the carbobenzoxy that replace arbitrarily, preferably have 1 to 3 on the benzyl ring, preferred especially 1 or 2 identical or different substituting group, substituting group can be various common substituting groups in the reactive compound chemistry.The preferred substituents that can narrate is: C
1-C
4Alkyl, C
1-C
4Alkoxyl, C
1-C
4Alkylthio group, C
1-C
4Haloalkyl, C
1-C
4Halogenated alkoxy, nitro, hydroxyl and halogen (preferred fluorine, chlorine and or bromine).
According to their special physics and/or chemical property, the mixture of the mixture of p-hydroxyphenylaceticacid and/or itself and other compound and/or insect killing substance and p-hydroxyphenylaceticacid and/or itself and other compound and the mixture of insect killing substance can be converted to common preparation, as solvent, emulsion, suspending agent, pulvis, foaming agent, paste, granule, aerosol is with natural and the synthetic material and the micro-fine capsule in polymer of reactive compound dipping.
These preparations are produced with known method, and for example, by with active component and auxiliary agent and/or filler, i.e. surfactant is at random used in liquid flux and/or solid carrier mixing and producing in the preparation, i.e. emulsifier and/or dispersant, and/or foam agent.Water is act as under the situation of filler, for example, also can be with an organic solvent as cosolvent.The liquid flux that is fit to mainly contains: aromatic hydrocarbon, and as dimethylbenzene, toluene or Fluhyzon, chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbon are as chlorobenzene, dichloroethane or carrene, aliphatic hydrocarbon, as thiacyclohexane or alkane, mineral oil fraction for example, alcohol, as butanols or ethylene glycol and ether and ester, ketone is as acetone, methyl. ethyl ketone, methyl. and isobutyl ketone or cyclohexanone, intensive polar solvent, as dimethyl formamide and dimethyl sulfoxide (DMSO), and water; The solid carrier that is fit to has: for example, the natural minerals powder is as kaolin, clay, talcum, chalk, quartz, Attagel, imvite or diatomite and synthetic mineral powder, as high dispersive silica, aluminium oxide and silicate; The solid carrier that is fit to granule has: for example, the natural rock of pulverizing and classification, as calcite, marble, float stone, sepiolite and dolomite, and the particle of inorganic synthetic particle and organic dust and organic material such as sawdust, shuck, corn ears and stems and tobacco stem; The emulsifier and/or the foam agent that are fit to have: for example nonionic and anion emulsifier, as polyoxyethylene fatty acid ester, polyoxyethylene aliphatic alcohol ether, for example alkylaryl polyglycol ether, alkylsulfonate, alkyl sulfate, arylsulphonate and albumin hydrolysate; The dispersant that is fit to has: for example lignin sulfite waste liquor and methylcellulose.
In preparation, can use adhesive such as carboxymethyl cellulose and powder, particle or latex shape synthetic polymer, as gum Arabic, polyvinyl alcohol and polyvinyl acetate, and natural phosphide such as cephalin and lecithin, and synthetic phospholipid.Other adhesives can be mineral oil and vegetable oil.
Colouring agent that may use such as inorganic pigment, for example iron oxide, titanium oxide and Prussia orchid and organic dyestuff, as alizarin dyes, azo dyes metal phthalocyanine dyestuff and trace nutrient, for example iron, manganese, boron, copper, cobalt, molybdenum and zinc salt.
In the poison bait preparation (preferred spreading poison bait preparation or solid poison bait preparation), said preparation also can contain lures cockroach and/or makes them take in other additives of desinsection disease substance.Spendable attractant and raising material are normally used in various preparations, as natural existence or synthetic material that produces and/or the easy material of taking in of cockroach, as contain starch, protein and/or the sugared product based on cereal or sugar.
Preparation preferably contains 0.001 to 95, particularly the mixture of the p-hydroxyphenylaceticacid of 0.01 to 70% weight and/or itself and other compound.
Preparation preferably contains (if be fit to, except that the mixture of p-hydroxyphenylaceticacid and/or itself and other compound) 0.1 to 95, the particularly insect killing substance of 0.5 to 90% weight.
The composition of control cockroach is to use in the mode of routine with the type of service that is fit to.
Illustrate the biologically active of the mixture of p-hydroxyphenylaceticacid and/or base and other compounds by following embodiment.
Embodiment A The improvement of bait effect
(covert in 2 relative corners in 2.25 * 4.70m) is put into another corner of drinking water and is put a slice of bread and do in the corner in the chamber.Put into 20 heros and 20 female cockroaches (Groton bug) after one day, will be for the bait tin that the contains insecticide (insecticidal active compound: the ethyl chlopyrifos of 0.5% weight) be placed on of picked-up apart from the wall limit at rusk 40cm place.
Bait or contain p-hydroxyphenylaceticacid, or untreated.
3 indoor bait tins of putting into processing, and 3 indoorly put into untreated bait tin.
Measure the lethality of buck and jenny in afterwards 3 days.
Result of the test:
Embodiment BThe improvement of nebulization in laboratory test
| Handle type | Per cent death loss % | ||
| The 1st day | The 2nd day | The 3rd day | |
| Contrast (insecticide is only arranged) | 22 | 42 | 52 |
| Insecticide+10mg p-hydroxyphenylaceticacid | 46 | 58 | 63 |
With contain (a) insecticidal active compound cyfloxylate or (b) aqueous spray solutions of cyfloxylate and p-hydroxyphenylaceticacid spray to ceramic tile so that the amount of application of cyfloxylate is every m
2The amount of application of 20mg reactive compound and p-hydroxyphenylaceticacid is every m
21mg.
Each all is placed in the corner of container (49 * 59cm, height 29.5cm) in the covert of containing water, food with above-mentioned ceramic tile, and puts into male in preceding 24 hours and female Groton bug (respectively 5) in operation.Each test repeats 5 times.
Result of the test
Embodiment C
| Handle type | Per cent death loss % | |
| The 1st day | The 2nd day | |
| Contrast (insecticide is only arranged) | 32 | 44 |
| Insecticide+p-hydroxyphenylaceticacid | 68 | 78 |
The improvement of nebulization in actual tests
Use in Australia and to contain (a) insecticidal active compound β-cyfloxylate or (b) β-cyfloxylate and p-hydroxyphenylaceticacid, make that the amount of application of β-cyfloxylate is every m
26.25mg reactive compound (half of recommended amounts), and the amount of application of p-hydroxyphenylaceticacid is every m
21mg.
Test is carried out on the plane of the non-constant of sanitary condition.Each preparation (β-cyfloxylate or β-cyfloxylate and p-hydroxyphenylaceticacid) is handled 7 to 8 groups.Measure activity by estimating the quantity of the catch of handling the bonding trap in preceding and processing back a period of time.
| Handle type | Reduced rate % after 7 days |
| Contrast (insecticide is only arranged) | 37 |
| Insecticide+p-hydroxyphenylaceticacid | 65 |
Claims (4)
1. Pesticidal combination, it comprises:
(A) insecticide of 0.1-95% weight reaches
(B) (i) p-hydroxyphenylaceticacid of 0.001-95% weight or its salt or the (ii) mixture of itself and other carboxylic acid, wherein the repellent action of composition A is reduced by composition B.
2. according to the Pesticidal combination of claim 1, it is characterized in that, except the mixture of the optional p-hydroxyphenylaceticacid that exists with salt form or itself and other carboxylic acid compound, they also contain carbamate, carboxylate, phosphate, phosphonate ester, Nitromethylene, nitro imino group, cyanoimino or cyano group methylene derivatives.
3. the method for Pesticidal combination of preparation claim 1, it comprises (i) p-hydroxyphenylaceticacid or its salt or (ii) it reaches the incremental agent of choosing wantonly with the mixture of other carboxylic acid with auxiliary agent and mixes.
4. claim 1 or 2 the Pesticidal combination purposes that is used to prevent and treat cockroach.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19528306A DE19528306A1 (en) | 1995-08-02 | 1995-08-02 | Para-hydroxyphenylacetic acid to reduce the repellency of insecticides |
| DE19528306.6 | 1995-08-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1148464A CN1148464A (en) | 1997-04-30 |
| CN1106146C true CN1106146C (en) | 2003-04-23 |
Family
ID=7768459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96112296A Expired - Fee Related CN1106146C (en) | 1995-08-02 | 1996-08-02 | P-hydroxy-phenylacetic acid for reducing anti-repelling properties of insecticide |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5741501A (en) |
| EP (1) | EP0756821B1 (en) |
| JP (1) | JP3963505B2 (en) |
| KR (1) | KR970009555A (en) |
| CN (1) | CN1106146C (en) |
| AR (1) | AR003075A1 (en) |
| AT (1) | ATE199627T1 (en) |
| AU (1) | AU702909B2 (en) |
| BG (1) | BG100761A (en) |
| BR (1) | BR9603254A (en) |
| CA (1) | CA2182349A1 (en) |
| DE (2) | DE19528306A1 (en) |
| ES (1) | ES2155157T3 (en) |
| GR (1) | GR3035866T3 (en) |
| HU (1) | HUP9602125A2 (en) |
| MX (1) | MX9603133A (en) |
| MY (1) | MY112982A (en) |
| NO (1) | NO963218L (en) |
| PL (1) | PL315467A1 (en) |
| PT (1) | PT756821E (en) |
| SV (1) | SV1996000066A (en) |
| TR (1) | TR199600607A2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110117153A1 (en) * | 2008-03-27 | 2011-05-19 | Christine Kritikou | Spinosyn bait formulations for the control of cockroaches and methods of using the same |
| CN111743885B (en) * | 2020-08-17 | 2022-03-15 | 山东省科学院生物研究所 | Application of p-hydroxyphenylacetic acid in preventing and/or treating cardiovascular diseases |
| CN113861154B (en) * | 2021-10-21 | 2022-09-13 | 华南师范大学 | Dihydroisomerin derivative and preparation method and application thereof |
| CN114903043B (en) * | 2022-04-28 | 2023-07-28 | 中国科学院昆明植物研究所 | Application of novel green pesticide |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5042053A (en) * | 1973-08-20 | 1975-04-16 | ||
| EP0588203A1 (en) * | 1992-09-18 | 1994-03-23 | Bayer Ag | Method and agent for the control of cockroaches |
| US5518719A (en) * | 1989-09-08 | 1996-05-21 | Burlington Bio-Medical & Scientific Corp. | Attractants and lures for cockroaches and palmettos |
-
1995
- 1995-08-02 DE DE19528306A patent/DE19528306A1/en not_active Withdrawn
-
1996
- 1996-07-22 AT AT96111748T patent/ATE199627T1/en not_active IP Right Cessation
- 1996-07-22 DE DE59606574T patent/DE59606574D1/en not_active Expired - Fee Related
- 1996-07-22 EP EP96111748A patent/EP0756821B1/en not_active Expired - Lifetime
- 1996-07-22 ES ES96111748T patent/ES2155157T3/en not_active Expired - Lifetime
- 1996-07-22 PT PT96111748T patent/PT756821E/en unknown
- 1996-07-24 TR TR96/00607A patent/TR199600607A2/en unknown
- 1996-07-26 JP JP21412096A patent/JP3963505B2/en not_active Expired - Fee Related
- 1996-07-26 US US08/690,286 patent/US5741501A/en not_active Expired - Fee Related
- 1996-07-29 AU AU60793/96A patent/AU702909B2/en not_active Ceased
- 1996-07-29 KR KR1019960030958A patent/KR970009555A/en not_active Application Discontinuation
- 1996-07-29 AR ARP960103795A patent/AR003075A1/en active IP Right Grant
- 1996-07-30 CA CA002182349A patent/CA2182349A1/en not_active Abandoned
- 1996-07-31 PL PL96315467A patent/PL315467A1/en unknown
- 1996-07-31 SV SV1996000066A patent/SV1996000066A/en unknown
- 1996-07-31 BG BG100761A patent/BG100761A/en unknown
- 1996-07-31 MY MYPI96003139A patent/MY112982A/en unknown
- 1996-08-01 NO NO963218A patent/NO963218L/en unknown
- 1996-08-01 BR BR9603254A patent/BR9603254A/en not_active IP Right Cessation
- 1996-08-01 HU HU9602125A patent/HUP9602125A2/en unknown
- 1996-08-01 MX MX9603133A patent/MX9603133A/en not_active IP Right Cessation
- 1996-08-02 CN CN96112296A patent/CN1106146C/en not_active Expired - Fee Related
-
2001
- 2001-05-15 GR GR20010400717T patent/GR3035866T3/en not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5042053A (en) * | 1973-08-20 | 1975-04-16 | ||
| US5518719A (en) * | 1989-09-08 | 1996-05-21 | Burlington Bio-Medical & Scientific Corp. | Attractants and lures for cockroaches and palmettos |
| EP0588203A1 (en) * | 1992-09-18 | 1994-03-23 | Bayer Ag | Method and agent for the control of cockroaches |
Also Published As
| Publication number | Publication date |
|---|---|
| US5741501A (en) | 1998-04-21 |
| MX9603133A (en) | 1997-03-29 |
| AR003075A1 (en) | 1998-05-27 |
| KR970009555A (en) | 1997-03-27 |
| PL315467A1 (en) | 1997-02-03 |
| HUP9602125A2 (en) | 1997-05-28 |
| DE59606574D1 (en) | 2001-04-19 |
| NO963218L (en) | 1997-02-03 |
| ATE199627T1 (en) | 2001-03-15 |
| JPH0940510A (en) | 1997-02-10 |
| JP3963505B2 (en) | 2007-08-22 |
| EP0756821A2 (en) | 1997-02-05 |
| MY112982A (en) | 2001-10-31 |
| CN1148464A (en) | 1997-04-30 |
| EP0756821B1 (en) | 2001-03-14 |
| BG100761A (en) | 1997-04-30 |
| GR3035866T3 (en) | 2001-08-31 |
| CA2182349A1 (en) | 1997-02-03 |
| NO963218D0 (en) | 1996-08-01 |
| EP0756821A3 (en) | 1997-11-26 |
| ES2155157T3 (en) | 2001-05-01 |
| SV1996000066A (en) | 1997-02-17 |
| AU6079396A (en) | 1997-02-06 |
| HU9602125D0 (en) | 1996-09-30 |
| BR9603254A (en) | 1998-04-28 |
| AU702909B2 (en) | 1999-03-11 |
| DE19528306A1 (en) | 1997-02-06 |
| TR199600607A2 (en) | 1997-02-21 |
| PT756821E (en) | 2001-08-30 |
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